


Ohhh Loverboy

by Demon_in_a_red_flannel



Series: 100 Kinks Challenge [2]
Category: Supernatural
Genre: #89 On a plane, 100 Kinks Challenge, Airplane, Airplane Sex, Dean is scared of flying, F/M, Hawaii, I Don't Even Know, Mile High Club, Oral Sex, Porn With Plot, Reader-Insert, Smut, So she distracts him, Some Dirty Dancing references?, Trying to get Dean onto other thoughts, Vacation, Vaginal Fingering
Language: English
Status: Completed
Published: 2018-05-21
Updated: 2018-05-21
Packaged: 2019-05-09 23:11:35
Rating: Mature
Warnings: Creator Chose Not To Use Archive Warnings
Chapters: 1
Words: 2,215
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/14725412
Author URL: https://archiveofourown.org/users/Demon_in_a_red_flannel/pseuds/Demon_in_a_red_flannel
Summary: I'm really horrible at summaries and honestly who gives a s***, this is smut. I guess nobody cares about the plot anyways xD  But for those who do: Dean is scared of flying and the reader tries do distract him





	Ohhh Loverboy

**Author's Note:**

> Enjoy! xo

„I fucking hate planes! Why the hell am I even doing this?“ Deans face was a mix between scared and angry as he made his way through the airport. Sam was right behind him, fighting with two large suitcases.“Come on man. You’ve crashed the Impala several times but have never been in a plane crash. Don’t you think there are other things you should be more afraid of?” Dean stopped dead in his tracks and Sam almost crashed into him. “Dude, not okay! Baby is the safest thing you will ever have the honor of sitting in!” Y/N let out an annoyed sigh. “Can’t you two just stop for once? After all the hunting we’ve done lately we really deserve this vacation! White beaches, cocktails, sexy shirtless surfer guys… Let’s hurry up and get the bags checked in, I don’t want to miss our flight!” Dean gave Sam another death stare and then continued walking.

Two hours later all three of them were sitting in their seats. Sam at the window so he could sleep, Y/N in the middle and Dean on the outside so he wouldn’t throw up on both of them in case he got nauseous. The flight attendands were currently going through the safety informations and Dean was listening carefully. Sam had already put on his neck pillow and sleeping mask and was starting to doze off before the plane had even started moving. Dean was shifting around nervously in his seat, fiddling with his hand and humming Stairway to Heaven. Y/N reached out for his shaking hand and started stroking it gently. “Hey, everything is going to be fine. We’ve had to deal with much worse things. As soon as we get up in the air we can get drunk and watch a movie, okay?” She gave him a reassuring smile. Dean nodded nervously. Sam started snoring loudly next to them. These were going to be the longest 8 hours of Y/N's life…

The plane began moving and Dean grabbed Y/N's arm with both of his hands, his fingers digging into the flesh. She smiled and interlaced her fingers with his. “Dean? Look at me.” The plane lost contact with the ground and started lifting off. His eyes were widened and his breathing was going fast. “Take a deep breath with me. In…” She closed her eyes and took a deep breath, Dean doing as she was. “…and out.” He slowly started to calm down. “You’re doing great, big boy. There’s really no reason to be scared. We’re probably the safest passengers on this plane anyways. If anything happens we can just call for Cas and he can woosh us right out of here.” He managed to give her a concerned smile and nodded. “You’re probably right…”

For the next 20 Minutes they both just sat there in silence, holding hands as the plane rose higher and higher. Y/N never thought Dean would actually be this terrified of flying. He was the strongest and most fearless one of the three of them, always running into situations guns blazing. On more than one occasion he would’ve given his life to protect her or Sam without even thinking. Seeing him this scared was equally funny and heartbreaking at the same time, like a big vicious guard dog being scared of thunder.

As soon as the seatbelt signs turned off, Dean shot up and somehow managed to get a whole bottle of whiskey and two cups from one of the stewardesses. “How the hell did you get that? That must’ve cost a fortune!” He handed the bottle and the cups to Y/N and sat back down, triple checking if his seatbelt was on securely. “You know I’m really good at flirting, right? Also my puppy eyes are irresistible.” he smirked and started filling the cups, emptying his first in one swig and refilling it a second time. “You doing okay?”.

“The thought of Hawaiian chicks in skirts and bikini tops is keeping me alive…”

“Well, that’s good to know.” Y/N laughed. “I don’t even think Sammy over here was still awake when we took off.” His mouth was half open, a thin streak of drool running into his messy hair. She grabbed her phone from her backpack under the seat and took a few photos of him, setting one as his new contact image. Dean sighed. “Do you want to watch a movie now? I think they even have _The Untouchables_ on here.”

“Man, I love that movie!” Y/N selected the movie and they both got comfortable.

Towards the end of the movie (the bottle of whiskey was already 2/3 empty) the stewardesses started distributing little pillows and blankets and the lights got dimmed down. Everyone around them was getting ready to sleep and it got quiet. “Do you want to sleep as well?” Y/N put a blanket over Sam and both of them and put up the armrest up, so she could lean her head onto Deans shoulder. “Nah, I may look calm on the outside but with all the adrenalin inside of me I don’t think I’ll be able to sleep…”

“That’s okay. I’m not tired anyways. Next movie-pick is mine though!” Y/N picked _Dirty Dancing_ and Dean smiled. He knew she had chosen it because Dean loved Swayze. He put his arm around her shoulder and she snuggled against his chest.

Baby and Johnny were just getting hot and steamy, dancing up against each other, when the plane started going through some turbulences. Dean shot straight up in his seat, his hands clawing into the armrest and Y/N thigh. “Fuck! I told you guys this wasnt safe!” He was hyperventilating. “Dean, calm down. This is totally normal. We’re going to be fine!”

“Nope, that’s it. I’m calling Cas!”

“Dean stop, please. Just try to calm down.” Dean didn’t listen. She caught a glimpse of what was going on in the movie at the moment and an idea came into her head.

“If you don’t listen to me I’m going to have to try and get you to calm down in another way!” Y/N looked around for a moment and when she saw everyone was sleeping she quickly slipped her hand under the blanket and in between his legs. She started slowly rubbing her palm against his cock and simultaneously began kissing his neck. “Y/N, what the-“ He couldn’t even finish his sentence when a deep moan escaped his throat. She chuckled quietly and brought her lips up to his ear, sucking gently on his earlobe. “I had to get you to calm down somehow. If you want me to stop just say the magic word. If you don’t you should stay quiet though, I don’t want everyone to hear us.” She could feel him getting hard under her hand, his jeans getting tighter. She fumbled with the button and when it finally popped open, she slid her hand into his pants and boxers. Dean shuddered when he felt her soft and warm hand on his dick, giving it a few careful pumps. His breathing was getting heavy and his eyes were closed, his head resting back against the seat. Y/N started moving her hand faster, while also trying to rub her thighs together to release some of her own pressure that had begun building up. Dean understood immediately and moved his hand from her thigh into her pants, his fingers working magic on her sensitive bundle of nerves. A ragged breath escaped her lips as he pushed his finger into her.

“Toilet, now!” was all she managed to whisper. Dean almost jumped up and Y/N had to grab his arm to signal him to stay quiet. He nodded and made his way to the toilet. A few minutes later she followed him. She made sure no one noticed and quietly knocked on the door. Dean almost forcefully pulled her in and as soon as she had locked the door he pushed her against the wall. Their lips crashed together in a needy kiss. His one hand grabbed her ass while his other one was grabbing a fistful of her hair, pulling her head back so he could attack her neck. He sucked and licked all the way from her collarbone to the sweet spot behind her ear, making her moan his name and grind against his leg. She grabbed his face and pulled it back to kiss her passionately, their tongues dancing together. After a while they pulled apart to catch their breath. “Are you okay with this?” She gave him a shy smile. “Oh hell yes, never been better.” He went in to kiss her again, but she quickly ducked away under his arm and spun him around, so he was being pressed against the wall now. She grinned at him mischievously and grabbed the hem of his shirt to pull it over his head. After he had helped her take it off and she had carefully placed it next to the sink she started kissing her way downwards. She slowly opened his pants and pulled them, together with his boxers, down to his ankles. His cock sprung free and slapped against his stomach. Dropping to her knees she started licking her way from the base to his tip, swirling her tongue around his head. Before she could take him in his mouth completely Dean reached down and grabbed her chin, sliding a thumb over her lips, which she started sucking into her mouth eagerly. She looked up at him trough her lashes as she continued and a deep growl vibrated trough his body. “As much as I want to fuck your pretty mouth and feel your little moans on my cock right now, I don’t think I would last long with all that teasing you’ve been doing.” He lifted her up and sat her down on the edge of the sink. “It’ll have to wait until next time.”

“What makes you so sure there will be a second time?” She smirked while tracing his abs with her fingers. “Trust me Baby, when I’m done not even a second or a third time will be enough for you.”

“Convince me then, Lover Boy.” She pulled him back in for a deep kiss, her fingers playing with the hair on the back of his neck. He slowly opened her blouse, taking a second to admire he beautiful black lace bra, before also taking it off and burying his face between her boobs. Y/N's head fell back against the mirror, unable to stop the moans spilling from her lips as he nibbled and licked her nipples, making sure to give both of them the same amount of attention.

“Dean, please-“

“What do you want me to do baby?”

“I-I need you to fuck me, I need to feel you inside of me!”

“Your wish is my command!” He helped her pull down her pants and panties and bent down to reach for his wallet to get a condom. “Fuck!” He stood back up and ran a hand through his hair. “What’s wrong?” “I didn’t pack a condom. Didn’t think I would need one…”

“Don’t worry, it’s fine. I have an IUD.”

“You sure?”

“Yes, please just fuck me already!” She pulled him close to her. Without another warning he slammed into her, moving at a brutal pace. The whole plane would’ve probably heard her screams if Dean hadn’t silenced her with his mouth. Her eyes rolled back into her head as he kept moving and moving and moving, not getting any slower. Her nails clawed into his back, almost drawing blood. He hissed, pain intensifying his pleasure even more.  “Tell me you’re close.” He managed to say in between his quiet grunts. Instead of answering she just nodded, unable to say a single coherent word. He could feel her already squeezing around him. She came hard, repeating his name over and over and over like a prayer as the explosive waves of her orgasm rippled through her. He came right after, his cock pulsing inside of her as they both tried to catch their breath again, their foreheads pressed together. “Wow…” was all she could say. Dean chuckled. "If flying was always like this, I could get used to it!" She laughed and slid off the sink, grabbing a few paper towels to clean herself. "Yeah, me too..." Dean had already cleaned himself up and was almost done putting his clothes back on. "So there's going to be another time?" He pushed a strand of her hair behind her ear. “We’ll see…” with that she grinned and pushed him out the door.

When she came back to their seats a few minutes later Dean was already half asleep. She carefully climbed over him and plopped herself down on her seat. All of the noise slowly woke Sam up. He lifted his sleeping mask and blinked sleepily. “Sorry, didn’t mean to wake you up…”

"I was waking up anyways, so it's no problem." He looked at Dean, who was now quietly snoring. “How the hell did you get him to fall asleep?” She shrugged and smiled. “You know I can be quite tiring sometimes.”

**Author's Note:**

> Please leave comments and suggestions on what I should write next, I'm always looking for new inspiration! :)  
> Kudos are also always appreciated <3  
> (If you found any grammar mistakes please let me know! English isn't my first language.)


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